#------------------------------------------------------------------------------
#$Date: 2025-10-06 13:36:51 +0300 (Mon, 06 Oct 2025) $
#$Revision: 302792 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/07/7160729.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7160729
loop_
_publ_author_name
'Jastrzębska, Katarzyna'
'Szymańska, Agata'
'Pawlak, Tomasz'
'Dolot, Rafał'
_publ_section_title
;
 Morpholino-based phosphorothioate analogs via oxathiaphospholane
 chemistry: synthesis, structural insights and stability.
;
_journal_issue                   38
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8755
_journal_page_last               8763
_journal_paper_doi               10.1039/d5ob01223f
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety
'C11 H17 N4 O5 P S2, 0.35(C1 H1 Cl3), 0.35(C2 H3 N1)'
_chemical_formula_sum            'C12.05 H18.4 Cl1.05 N4.35 O5 P S2'
_chemical_formula_weight         436.52
_chemical_name_common            OTP-N-mU-1
_chemical_name_systematic        OTP-N-mU-1
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-07-08
_audit_creation_method
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_audit_update_record
;
2025-07-08 deposited with the CCDC.	2025-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.621(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0836(3)
_cell_length_b                   7.22770(10)
_cell_length_c                   17.8604(3)
_cell_measurement_reflns_used    26147
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      79.0550
_cell_measurement_theta_min      2.6770
_cell_volume                     2035.66(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.122a 64-bit (release 15-05-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  25.00   0.50    0.22    --  -47.34  59.00 138.00  176
  2  ω   -119.00 -32.00   0.50    0.22    --  -47.34 -59.00  -0.00  174
  3  ω     32.00 119.00   0.50    0.22    --   47.34  59.00 138.00  174
  4  ω    -24.00  63.00   0.50    0.22    --   47.34 -59.00  -0.00  174
  5  ω    -68.00 -19.00   0.50    0.87    --  -91.75  59.00 138.00   98
  6  ω   -163.00 -76.00   0.50    0.87    --  -91.75 -59.00  -0.00  174
  7  ω     98.00 178.00   0.50    0.87    --  113.25  59.00 138.00  160
  8  ω     42.00  68.00   0.50    0.87    --  113.25 -59.00  -0.00   52
  9  ω    -26.00  28.00   0.50    0.22    --  -47.34  19.00 -60.00  108
 10  ω     34.00  93.00   0.50    0.22    --   47.34-125.00-180.00  118
 11  ω     33.00 119.00   0.50    0.22    --   47.34  57.00-120.00  172
 12  ω   -163.00 -75.00   0.50    0.87    --  -91.75 -61.00-120.00  176
 13  ω   -163.00 -79.00   0.50    0.87    --  -91.75 -45.00 -60.00  168
 14  ω   -163.00 -69.00   0.50    0.87    --  -91.75 -77.00-150.00  188
 15  ω   -163.00 -69.00   0.50    0.87    --  -91.75 -77.00-120.00  188
 16  ω   -166.00 -78.00   0.50    0.87    --  -91.75 -15.00-120.00  176
 17  ω   -163.00 -69.00   0.50    0.87    --  -91.75 -77.00 -90.00  188
 18  ω   -163.00 -69.00   0.50    0.87    --  -91.75 -77.00-120.00  188
 19  ω    -51.00 -20.00   0.50    0.87    --  -91.75  45.00 -90.00   62
 20  ω    -51.00 -20.00   0.50    0.87    --  -91.75  45.00 -60.00   62
 21  ω   -163.00 -69.00   0.50    0.87    --  -91.75 -77.00 -90.00  188
 22  ω    -71.00 -19.00   0.50    0.87    --  -91.75  61.00  60.00  104
 23  ω   -163.00 -79.00   0.50    0.87    --  -91.75 -45.00 -60.00  168
 24  ω     96.00 156.00   0.50    0.87    --  113.25 125.00 150.00  120
 25  ω    101.00 148.00   0.50    0.87    --  113.25  45.00-120.00   94
 26  ω     43.00 104.00   0.50    0.87    --  113.25 -95.00 120.00  122
 27  ω     42.00  67.00   0.50    0.87    --  113.25 -61.00-150.00   50
 28  ω    146.00 172.00   0.50    0.87    --  113.25  61.00 -90.00   52
 29  ω     43.00  70.00   0.50    0.87    --  113.25 -61.00  30.00   54
 30  ω     98.00 141.00   0.50    0.87    --  113.25  61.00 -90.00   86
 31  ω    101.00 177.00   0.50    0.87    --  113.25  45.00-150.00  152
 32  ω     96.00 176.00   0.50    0.87    --  113.25  77.00  30.00  160
 33  ω     96.00 177.00   0.50    0.87    --  113.25 125.00-150.00  162
 34  ω    126.00 176.00   0.50    0.87    --  113.25 125.00  60.00  100
 35  ω    153.00 178.00   0.50    0.87    --  113.25  77.00  60.00   50
 36  ω     42.00  70.00   0.50    0.87    --  113.25 -61.00 120.00   56
 37  ω    144.00 170.00   0.50    0.87    --  113.25  77.00 -60.00   52
 38  ω    102.00 146.00   0.50    0.87    --  113.25  77.00 -90.00   88
 39  ω    114.00 141.00   0.50    0.87    --  113.25  77.00 -60.00   54
 40  ω    114.00 139.00   0.50    0.87    --  113.25  77.00  60.00   50
 41  ω    110.00 159.00   0.50    0.87    --  113.25  45.00-180.00   98
 42  ω     45.00  71.00   0.50    0.87    --  113.25 -61.00 -60.00   52
 43  ω     43.00  89.00   0.50    0.87    --  113.25 -95.00-180.00   92
 44  ω    101.00 154.00   0.50    0.87    --  113.25  15.00  60.00  106
 45  ω     45.00 110.00   0.50    0.87    --  113.25-125.00 120.00  130
 46  ω     42.00 105.00   0.50    0.87    --  113.25 -95.00 -30.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0632338000
_diffrn_orient_matrix_UB_12      0.0537136000
_diffrn_orient_matrix_UB_13      -0.0853622000
_diffrn_orient_matrix_UB_21      0.0646301000
_diffrn_orient_matrix_UB_22      0.1395149000
_diffrn_orient_matrix_UB_23      -0.0076956000
_diffrn_orient_matrix_UB_31      0.0371394000
_diffrn_orient_matrix_UB_32      -0.1519106000
_diffrn_orient_matrix_UB_33      -0.0371858000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38701
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.318
_diffrn_reflns_theta_min         2.680
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.122a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_recrystallization_method
're-crystallized from chloroform : acetonitrile : hexane 7:2:1 (v/v/v) mixture,'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.619
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details
;
 Flack x determined using 3343 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         8524
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1131P)²+1.4527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1637
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                7961
_reflns_number_total             8524
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob01223f2.cif
_cod_data_source_block           kj_mun_fast_02_autored
_cod_depositor_comments          'Adding full bibliography for 7160729.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C12.05 H18.40 Cl1.05 N4.35 O5 P S2'
_cod_database_code               7160729
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S P'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.800
_shelx_estimated_absorpt_t_min   0.388
_diffrn_oxdiff_digest_hkl
;
43b7782016fc1886edf1a9c0ecbd4a036314df
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: Cl02(0.7) Cl01(0.7) Cl03(0.7) C1(0.7) H1(0.7) C02(0.7) N03(0.7)
 C01(0.7) H01A(0.7) H01B(0.7) H01C(0.7)
3.a Ternary CH refined with riding coordinates:
 C106(H106), C102(H102), C206(H206), C202(H202), C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C105(H10B,H10C), C113(H11A,H11B), C103(H10D,H10E), C205(H20A,H20B), C213(H21A,
 H21B), C114(H11C,H11D), C203(H20C,H20D), C115(H11E,H11F), C214(H21C,H21D),
 C215(H21E,H21F)
3.c Aromatic/amide H refined with riding coordinates:
 N38(H38), N109(H109), N209(H209), C112(H112), C111(H111), C212(H212),
 C211(H211)
3.d Idealised Me refined as rotating group:
 C01(H01A,H01B,H01C)
3.e Idealised tetrahedral OH refined as rotating group:
 O105(H105), O205(H205)
;
_olex2_exptl_crystal_mounting_method
'mounted on a nylon cryo-loop with mineral oil as a cryoprotectant'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.200
_oxdiff_exptl_absorpt_empirical_full_min 0.638
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P101 P 0.67351(7) 0.90152(18) 0.08923(7) 0.0272(3) Uani 1 1 d . . . . .
S102 S 0.66119(8) 1.15734(18) 0.05468(7) 0.0328(3) Uani 1 1 d . . . . .
S101 S 0.57947(9) 0.80572(19) 0.12754(9) 0.0374(3) Uani 1 1 d . . . . .
P201 P 0.82620(8) 0.6732(2) -0.08066(7) 0.0313(3) Uani 1 1 d . . . . .
S202 S 0.83538(8) 0.9144(2) -0.03134(9) 0.0389(3) Uani 1 1 d . . . . .
S201 S 0.89719(9) 0.6359(3) -0.15162(9) 0.0450(4) Uani 1 1 d . . . . .
Cl02 Cl 0.73577(16) -0.1015(4) -0.33328(18) 0.0585(6) Uani 0.7 1 d . . P . .
Cl01 Cl 0.89771(16) 0.0681(5) -0.3057(2) 0.0721(8) Uani 0.7 1 d . . P . .
O101 O 0.8904(2) 0.4021(6) 0.2880(2) 0.0316(7) Uani 1 1 d . . . . .
O201 O 0.6098(2) 0.1758(6) -0.2780(2) 0.0348(8) Uani 1 1 d . . . . .
O105 O 0.9173(3) 0.0895(6) 0.2000(2) 0.0360(8) Uani 1 1 d . . . . .
H105 H 0.948511 0.084208 0.249583 0.054 Uiso 1 1 calc R U . . .
O104 O 0.6605(2) 0.7459(5) 0.0202(2) 0.0321(8) Uani 1 1 d . . . . .
O205 O 0.5798(3) -0.1568(6) -0.2044(2) 0.0398(9) Uani 1 1 d . . . . .
H205 H 0.543214 -0.158642 -0.252045 0.060 Uiso 1 1 calc R U . . .
O204 O 0.8622(3) 0.4971(6) -0.0221(2) 0.0371(8) Uani 1 1 d . . . . .
N104 N 0.7840(3) 0.6866(6) 0.1937(2) 0.0319(9) Uani 1 1 d . . . . .
Cl03 Cl 0.8085(5) -0.0698(9) -0.4610(3) 0.149(3) Uani 0.7 1 d . . P . .
N105 N 0.7661(3) 0.8671(7) 0.1612(3) 0.0324(9) Uani 1 1 d . . . . .
O103 O 0.9664(4) 0.5118(9) 0.6469(3) 0.0656(16) Uani 1 1 d . . . . .
N204 N 0.7099(3) 0.4502(7) -0.1743(3) 0.0337(10) Uani 1 1 d . . . . .
N107 N 0.8729(3) 0.4977(7) 0.4040(3) 0.0357(10) Uani 1 1 d . . . . .
O102 O 0.7442(3) 0.4309(12) 0.4099(3) 0.0689(18) Uani 1 1 d . . . . .
N207 N 0.6181(3) 0.3125(8) -0.3910(3) 0.0387(10) Uani 1 1 d . . . . .
O202 O 0.7443(3) 0.3841(10) -0.3974(2) 0.0586(13) Uani 1 1 d . . . . .
N38 N 0.7266(3) 0.6188(7) -0.1303(3) 0.0350(10) Uani 1 1 d . . . . .
H38 H 0.685336 0.690843 -0.129675 0.042 Uiso 1 1 calc R U . . .
N109 N 0.8594(4) 0.4658(8) 0.5275(3) 0.0462(12) Uani 1 1 d . . . . .
H109 H 0.827755 0.438101 0.554866 0.055 Uiso 1 1 calc R U . . .
O203 O 0.5151(4) 0.3254(10) -0.6333(3) 0.0701(16) Uani 1 1 d . . . . .
N209 N 0.6273(4) 0.3553(9) -0.5150(3) 0.0499(14) Uani 1 1 d . . . . .
H209 H 0.658476 0.379929 -0.543176 0.060 Uiso 1 1 calc R U . . .
C106 C 0.8530(3) 0.3909(8) 0.2000(3) 0.0298(10) Uani 1 1 d . . . . .
H106 H 0.796589 0.328267 0.182963 0.036 Uiso 1 1 calc R U . . .
C105 C 0.8405(3) 0.5843(8) 0.1637(3) 0.0311(10) Uani 1 1 d . . . . .
H10B H 0.895825 0.648366 0.179996 0.037 Uiso 1 1 calc R U . . .
H10C H 0.815032 0.577013 0.103752 0.037 Uiso 1 1 calc R U . . .
C102 C 0.8345(3) 0.4999(8) 0.3149(3) 0.0339(11) Uani 1 1 d . . . . .
H102 H 0.778790 0.434159 0.296080 0.041 Uiso 1 1 calc R U . . .
C113 C 0.9107(4) 0.2755(8) 0.1734(3) 0.0340(11) Uani 1 1 d . . . . .
H11A H 0.889496 0.277089 0.113412 0.041 Uiso 1 1 calc R U . . .
H11B H 0.967964 0.331839 0.194478 0.041 Uiso 1 1 calc R U . . .
C112 C 0.9572(4) 0.5344(8) 0.4450(4) 0.0394(12) Uani 1 1 d . . . . .
H112 H 0.991346 0.555850 0.414565 0.047 Uiso 1 1 calc R U . . .
C206 C 0.6460(3) 0.1458(9) -0.1911(3) 0.0335(11) Uani 1 1 d . . . . .
H206 H 0.701931 0.081589 -0.175553 0.040 Uiso 1 1 calc R U . . .
C111 C 0.9938(4) 0.5416(9) 0.5261(4) 0.0420(13) Uani 1 1 d . . . . .
H111 H 1.052498 0.568986 0.552310 0.050 Uiso 1 1 calc R U . . .
C110 C 0.9434(5) 0.5075(9) 0.5730(4) 0.0460(14) Uani 1 1 d . . . . .
C103 C 0.8206(4) 0.6976(9) 0.2828(3) 0.0370(12) Uani 1 1 d . . . . .
H10D H 0.781394 0.763478 0.302474 0.044 Uiso 1 1 calc R U . . .
H10E H 0.875113 0.765498 0.301590 0.044 Uiso 1 1 calc R U . . .
C205 C 0.6582(3) 0.3293(8) -0.1465(3) 0.0333(11) Uani 1 1 d . . . . .
H20A H 0.602463 0.387597 -0.157419 0.040 Uiso 1 1 calc R U . . .
H20B H 0.686664 0.308752 -0.087314 0.040 Uiso 1 1 calc R U . . .
C202 C 0.6606(4) 0.2958(9) -0.3015(3) 0.0377(12) Uani 1 1 d . . . . .
H202 H 0.718127 0.240271 -0.287037 0.045 Uiso 1 1 calc R U . . .
C213 C 0.5847(4) 0.0229(8) -0.1721(3) 0.0357(11) Uani 1 1 d . . . . .
H21A H 0.602656 0.014092 -0.112460 0.043 Uiso 1 1 calc R U . . .
H21B H 0.527721 0.080101 -0.194183 0.043 Uiso 1 1 calc R U . . .
C208 C 0.6683(4) 0.3520(11) -0.4329(4) 0.0473(15) Uani 1 1 d . . . . .
C108 C 0.8203(4) 0.4628(11) 0.4450(3) 0.0462(15) Uani 1 1 d . . . . .
C212 C 0.5321(4) 0.2867(9) -0.4294(3) 0.0429(13) Uani 1 1 d . . . . .
H212 H 0.498960 0.265040 -0.398015 0.051 Uiso 1 1 calc R U . . .
C210 C 0.5424(5) 0.3244(10) -0.5589(4) 0.0514(16) Uani 1 1 d . . . . .
C114 C 0.5869(3) 0.6306(8) -0.0012(3) 0.0344(11) Uani 1 1 d . . . . .
H11C H 0.595801 0.514866 -0.026434 0.041 Uiso 1 1 calc R U . . .
H11D H 0.537142 0.695421 -0.040824 0.041 Uiso 1 1 calc R U . . .
C203 C 0.6688(4) 0.4832(9) -0.2617(3) 0.0384(12) Uani 1 1 d . . . . .
H20C H 0.703611 0.566991 -0.280093 0.046 Uiso 1 1 calc R U . . .
H20D H 0.612213 0.539898 -0.275212 0.046 Uiso 1 1 calc R U . . .
C211 C 0.4942(5) 0.2919(10) -0.5109(4) 0.0494(15) Uani 1 1 d . . . . .
H211 H 0.434688 0.273521 -0.536482 0.059 Uiso 1 1 calc R U . . .
C115 C 0.5709(4) 0.5861(8) 0.0745(4) 0.0370(11) Uani 1 1 d . . . . .
H11E H 0.613501 0.496796 0.108986 0.044 Uiso 1 1 calc R U . . .
H11F H 0.513682 0.532114 0.060169 0.044 Uiso 1 1 calc R U . . .
C214 C 0.9346(4) 0.4040(10) -0.0256(4) 0.0443(13) Uani 1 1 d . . . . .
H21C H 0.936841 0.275669 -0.005499 0.053 Uiso 1 1 calc R U . . .
H21D H 0.987042 0.468515 0.009413 0.053 Uiso 1 1 calc R U . . .
C215 C 0.9289(4) 0.4015(11) -0.1127(4) 0.0480(14) Uani 1 1 d . . . . .
H21E H 0.886298 0.309932 -0.145253 0.058 Uiso 1 1 calc R U . . .
H21F H 0.984465 0.369316 -0.114557 0.058 Uiso 1 1 calc R U . . .
C1 C 0.8280(9) -0.1064(16) -0.3569(6) 0.062(3) Uani 0.7 1 d . . P . .
H1 H 0.856936 -0.228546 -0.339799 0.074 Uiso 0.7 1 calc R U P . .
C02 C 0.3661(14) 0.556(4) -0.3082(11) 0.123(8) Uani 0.7 1 d . . P . .
N03 N 0.3545(10) 0.422(3) -0.3624(10) 0.115(6) Uani 0.7 1 d . . P . .
H10A H 0.799(4) 0.940(9) 0.166(4) 0.023(15) Uiso 1 1 d . . . . .
C01 C 0.3833(7) 0.6935(18) -0.2538(6) 0.059(3) Uani 0.7 1 d . . P . .
H01A H 0.371502 0.812531 -0.282253 0.088 Uiso 0.7 1 calc R U P . .
H01B H 0.443244 0.688060 -0.217400 0.088 Uiso 0.7 1 calc R U P . .
H01C H 0.347821 0.680442 -0.222160 0.088 Uiso 0.7 1 calc R U P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S102 P101 S101 114.69(8) . . ?
O104 P101 S102 117.05(15) . . ?
O104 P101 S101 96.96(14) . . ?
O104 P101 N105 107.6(2) . . ?
N105 P101 S102 110.57(19) . . ?
N105 P101 S101 109.01(19) . . ?
C115 S101 P101 92.12(18) . . ?
S202 P201 S201 115.48(9) . . ?
O204 P201 S202 118.24(16) . . ?
O204 P201 S201 97.25(16) . . ?
O204 P201 N38 102.7(2) . . ?
N38 P201 S202 110.41(19) . . ?
N38 P201 S201 111.56(18) . . ?
C215 S201 P201 92.6(2) . . ?
C102 O101 C106 108.8(4) . . ?
C202 O201 C206 110.8(4) . . ?
C113 O105 H105 109.5 . . ?
C114 O104 P101 117.1(3) . . ?
C213 O205 H205 109.5 . . ?
C214 O204 P201 117.7(4) . . ?
N105 N104 C105 112.6(4) . . ?
N105 N104 C103 109.2(4) . . ?
C105 N104 C103 110.9(4) . . ?
P101 N105 H10A 116(5) . . ?
N104 N105 P101 117.2(4) . . ?
N104 N105 H10A 125(5) . . ?
N38 N204 C205 110.2(4) . . ?
N38 N204 C203 111.3(4) . . ?
C205 N204 C203 110.8(4) . . ?
C112 N107 C102 121.1(5) . . ?
C112 N107 C108 121.1(5) . . ?
C108 N107 C102 117.7(5) . . ?
C208 N207 C202 117.2(5) . . ?
C208 N207 C212 122.1(5) . . ?
C212 N207 C202 120.8(5) . . ?
P201 N38 H38 121.5 . . ?
N204 N38 P201 116.9(4) . . ?
N204 N38 H38 121.5 . . ?
C110 N109 H109 116.4 . . ?
C108 N109 H109 116.4 . . ?
C108 N109 C110 127.2(6) . . ?
C208 N209 H209 116.5 . . ?
C208 N209 C210 127.1(6) . . ?
C210 N209 H209 116.5 . . ?
O101 C106 H106 109.0 . . ?
O101 C106 C105 109.9(4) . . ?
O101 C106 C113 107.7(4) . . ?
C105 C106 H106 109.0 . . ?
C113 C106 H106 109.0 . . ?
C113 C106 C105 112.1(4) . . ?
N104 C105 C106 108.1(4) . . ?
N104 C105 H10B 110.1 . . ?
N104 C105 H10C 110.1 . . ?
C106 C105 H10B 110.1 . . ?
C106 C105 H10C 110.1 . . ?
H10B C105 H10C 108.4 . . ?
O101 C102 N107 106.5(4) . . ?
O101 C102 H102 109.2 . . ?
O101 C102 C103 111.7(4) . . ?
N107 C102 H102 109.2 . . ?
N107 C102 C103 111.0(4) . . ?
C103 C102 H102 109.2 . . ?
O105 C113 C106 113.4(4) . . ?
O105 C113 H11A 108.9 . . ?
O105 C113 H11B 108.9 . . ?
C106 C113 H11A 108.9 . . ?
C106 C113 H11B 108.9 . . ?
H11A C113 H11B 107.7 . . ?
N107 C112 H112 118.5 . . ?
C111 C112 N107 122.9(6) . . ?
C111 C112 H112 118.5 . . ?
O201 C206 H206 109.6 . . ?
O201 C206 C205 110.3(5) . . ?
O201 C206 C213 106.4(4) . . ?
C205 C206 H206 109.6 . . ?
C213 C206 H206 109.6 . . ?
C213 C206 C205 111.3(4) . . ?
C112 C111 H111 120.4 . . ?
C112 C111 C110 119.3(6) . . ?
C110 C111 H111 120.4 . . ?
O103 C110 N109 117.9(6) . . ?
O103 C110 C111 127.6(6) . . ?
N109 C110 C111 114.5(5) . . ?
N104 C103 C102 107.2(4) . . ?
N104 C103 H10D 110.3 . . ?
N104 C103 H10E 110.3 . . ?
C102 C103 H10D 110.3 . . ?
C102 C103 H10E 110.3 . . ?
H10D C103 H10E 108.5 . . ?
N204 C205 C206 108.9(4) . . ?
N204 C205 H20A 109.9 . . ?
N204 C205 H20B 109.9 . . ?
C206 C205 H20A 109.9 . . ?
C206 C205 H20B 109.9 . . ?
H20A C205 H20B 108.3 . . ?
O201 C202 N207 105.7(4) . . ?
O201 C202 H202 109.6 . . ?
O201 C202 C203 111.8(4) . . ?
N207 C202 H202 109.6 . . ?
N207 C202 C203 110.6(5) . . ?
C203 C202 H202 109.6 . . ?
O205 C213 C206 112.8(4) . . ?
O205 C213 H21A 109.0 . . ?
O205 C213 H21B 109.0 . . ?
C206 C213 H21A 109.0 . . ?
C206 C213 H21B 109.0 . . ?
H21A C213 H21B 107.8 . . ?
O202 C208 N207 121.1(5) . . ?
O202 C208 N209 123.9(6) . . ?
N209 C208 N207 115.0(6) . . ?
O102 C108 N107 122.6(5) . . ?
O102 C108 N109 122.5(6) . . ?
N109 C108 N107 114.9(6) . . ?
N207 C212 H212 119.6 . . ?
C211 C212 N207 120.8(6) . . ?
C211 C212 H212 119.6 . . ?
O203 C210 N209 119.5(7) . . ?
O203 C210 C211 126.0(7) . . ?
N209 C210 C211 114.4(5) . . ?
O104 C114 H11C 109.9 . . ?
O104 C114 H11D 109.9 . . ?
O104 C114 C115 109.1(4) . . ?
H11C C114 H11D 108.3 . . ?
C115 C114 H11C 109.9 . . ?
C115 C114 H11D 109.9 . . ?
N204 C203 C202 106.0(5) . . ?
N204 C203 H20C 110.5 . . ?
N204 C203 H20D 110.5 . . ?
C202 C203 H20C 110.5 . . ?
C202 C203 H20D 110.5 . . ?
H20C C203 H20D 108.7 . . ?
C212 C211 C210 120.6(6) . . ?
C212 C211 H211 119.7 . . ?
C210 C211 H211 119.7 . . ?
S101 C115 H11E 110.6 . . ?
S101 C115 H11F 110.6 . . ?
C114 C115 S101 105.8(4) . . ?
C114 C115 H11E 110.6 . . ?
C114 C115 H11F 110.6 . . ?
H11E C115 H11F 108.7 . . ?
O204 C214 H21C 109.8 . . ?
O204 C214 H21D 109.8 . . ?
O204 C214 C215 109.5(5) . . ?
H21C C214 H21D 108.2 . . ?
C215 C214 H21C 109.8 . . ?
C215 C214 H21D 109.8 . . ?
S201 C215 H21E 110.6 . . ?
S201 C215 H21F 110.6 . . ?
C214 C215 S201 105.7(5) . . ?
C214 C215 H21E 110.6 . . ?
C214 C215 H21F 110.6 . . ?
H21E C215 H21F 108.7 . . ?
Cl02 C1 H1 108.8 . . ?
Cl01 C1 Cl02 110.5(5) . . ?
Cl01 C1 Cl03 105.0(7) . . ?
Cl01 C1 H1 108.8 . . ?
Cl03 C1 Cl02 114.7(7) . . ?
Cl03 C1 H1 108.8 . . ?
N03 C02 C01 176(2) . . ?
C02 C01 H01A 109.5 . . ?
C02 C01 H01B 109.5 . . ?
C02 C01 H01C 109.5 . . ?
H01A C01 H01B 109.5 . . ?
H01A C01 H01C 109.5 . . ?
H01B C01 H01C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P101 S102 1.9350(19) . ?
P101 S101 2.0914(18) . ?
P101 O104 1.620(4) . ?
P101 N105 1.629(5) . ?
S101 C115 1.825(6) . ?
P201 S202 1.933(2) . ?
P201 S201 2.0812(18) . ?
P201 O204 1.611(4) . ?
P201 N38 1.635(5) . ?
S201 C215 1.832(8) . ?
Cl02 C1 1.782(12) . ?
Cl01 C1 1.734(15) . ?
O101 C106 1.453(5) . ?
O101 C102 1.411(7) . ?
O201 C206 1.448(6) . ?
O201 C202 1.400(7) . ?
O105 H105 0.8400 . ?
O105 C113 1.416(7) . ?
O104 C114 1.432(6) . ?
O205 H205 0.8400 . ?
O205 C213 1.411(7) . ?
O204 C214 1.430(7) . ?
N104 N105 1.413(6) . ?
N104 C105 1.471(7) . ?
N104 C103 1.471(6) . ?
Cl03 C1 1.778(11) . ?
N105 H10A 0.75(7) . ?
O103 C110 1.225(7) . ?
N204 N38 1.418(7) . ?
N204 C205 1.458(7) . ?
N204 C203 1.464(7) . ?
N107 C102 1.470(6) . ?
N107 C112 1.367(8) . ?
N107 C108 1.384(8) . ?
O102 C108 1.228(8) . ?
N207 C202 1.486(7) . ?
N207 C208 1.368(8) . ?
N207 C212 1.374(8) . ?
O202 C208 1.229(8) . ?
N38 H38 0.8800 . ?
N109 H109 0.8800 . ?
N109 C110 1.383(9) . ?
N109 C108 1.365(7) . ?
O203 C210 1.229(8) . ?
N209 H209 0.8800 . ?
N209 C208 1.360(7) . ?
N209 C210 1.376(10) . ?
C106 H106 1.0000 . ?
C106 C105 1.521(8) . ?
C106 C113 1.502(8) . ?
C105 H10B 0.9900 . ?
C105 H10C 0.9900 . ?
C102 H102 1.0000 . ?
C102 C103 1.524(8) . ?
C113 H11A 0.9900 . ?
C113 H11B 0.9900 . ?
C112 H112 0.9500 . ?
C112 C111 1.341(8) . ?
C206 H206 1.0000 . ?
C206 C205 1.520(8) . ?
C206 C213 1.508(8) . ?
C111 H111 0.9500 . ?
C111 C110 1.434(9) . ?
C103 H10D 0.9900 . ?
C103 H10E 0.9900 . ?
C205 H20A 0.9900 . ?
C205 H20B 0.9900 . ?
C202 H202 1.0000 . ?
C202 C203 1.511(9) . ?
C213 H21A 0.9900 . ?
C213 H21B 0.9900 . ?
C212 H212 0.9500 . ?
C212 C211 1.348(8) . ?
C210 C211 1.417(11) . ?
C114 H11C 0.9900 . ?
C114 H11D 0.9900 . ?
C114 C115 1.514(8) . ?
C203 H20C 0.9900 . ?
C203 H20D 0.9900 . ?
C211 H211 0.9500 . ?
C115 H11E 0.9900 . ?
C115 H11F 0.9900 . ?
C214 H21C 0.9900 . ?
C214 H21D 0.9900 . ?
C214 C215 1.521(9) . ?
C215 H21E 0.9900 . ?
C215 H21F 0.9900 . ?
C1 H1 1.0000 . ?
C02 N03 1.33(3) . ?
C02 C01 1.34(3) . ?
C01 H01A 0.9800 . ?
C01 H01B 0.9800 . ?
C01 H01C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O105 H105 O103 0.84 1.93 2.748(6) 163.4 2_746 yes
O205 H205 O203 0.84 1.90 2.725(6) 165.3 2_644 yes
N38 H38 O205 0.88 2.10 2.850(6) 143.2 1_565 yes
N109 H109 O202 0.88 1.96 2.836(7) 172.5 1_556 yes
N209 H209 O102 0.88 1.98 2.855(7) 171.0 1_554 yes
N105 H10A O105 0.75(7) 2.17(7) 2.892(6) 163(6) 1_565 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P101 S101 C115 C114 -33.9(4) . . . . ?
P101 O104 C114 C115 -38.1(5) . . . . ?
S102 P101 O104 C114 -111.2(3) . . . . ?
S102 P101 N105 N104 179.1(3) . . . . ?
S101 P101 O104 C114 11.1(4) . . . . ?
S101 P101 N105 N104 52.2(4) . . . . ?
P201 S201 C215 C214 -32.2(4) . . . . ?
P201 O204 C214 C215 -36.9(7) . . . . ?
S202 P201 O204 C214 -113.0(4) . . . . ?
S202 P201 N38 N204 176.0(3) . . . . ?
S201 P201 O204 C214 11.1(4) . . . . ?
S201 P201 N38 N204 46.2(4) . . . . ?
O101 C106 C105 N104 -59.7(5) . . . . ?
O101 C106 C113 O105 64.5(6) . . . . ?
O101 C102 C103 N104 60.0(6) . . . . ?
O201 C206 C205 N204 -55.6(5) . . . . ?
O201 C206 C213 O205 67.1(6) . . . . ?
O201 C202 C203 N204 61.6(6) . . . . ?
O104 P101 N105 N104 -51.9(4) . . . . ?
O104 C114 C115 S101 47.0(5) . . . . ?
O204 P201 N38 N204 -57.0(4) . . . . ?
O204 C214 C215 S201 44.9(6) . . . . ?
N105 P101 O104 C114 123.7(4) . . . . ?
N105 N104 C105 C106 -178.0(4) . . . . ?
N105 N104 C103 C102 177.1(4) . . . . ?
N107 C102 C103 N104 178.7(4) . . . . ?
N107 C112 C111 C110 0.7(10) . . . . ?
N207 C202 C203 N204 179.1(4) . . . . ?
N207 C212 C211 C210 -0.1(11) . . . . ?
N38 P201 O204 C214 125.2(4) . . . . ?
N38 N204 C205 C206 -176.6(4) . . . . ?
N38 N204 C203 C202 175.8(4) . . . . ?
O203 C210 C211 C212 177.2(8) . . . . ?
N209 C210 C211 C212 -2.2(10) . . . . ?
C106 O101 C102 N107 176.7(4) . . . . ?
C106 O101 C102 C103 -61.9(5) . . . . ?
C105 N104 N105 P101 103.2(5) . . . . ?
C105 N104 C103 C102 -58.3(6) . . . . ?
C105 C106 C113 O105 -174.4(4) . . . . ?
C102 O101 C106 C105 61.3(5) . . . . ?
C102 O101 C106 C113 -176.3(4) . . . . ?
C102 N107 C112 C111 177.0(6) . . . . ?
C102 N107 C108 O102 1.4(11) . . . . ?
C102 N107 C108 N109 -178.9(5) . . . . ?
C113 C106 C105 N104 -179.5(4) . . . . ?
C112 N107 C102 O101 45.2(7) . . . . ?
C112 N107 C102 C103 -76.6(6) . . . . ?
C112 N107 C108 O102 179.4(7) . . . . ?
C112 N107 C108 N109 -0.9(9) . . . . ?
C112 C111 C110 O103 -178.6(7) . . . . ?
C112 C111 C110 N109 1.2(9) . . . . ?
C206 O201 C202 N207 178.9(4) . . . . ?
C206 O201 C202 C203 -60.7(6) . . . . ?
C110 N109 C108 N107 3.2(10) . . . . ?
C110 N109 C108 O102 -177.1(8) . . . . ?
C103 N104 N105 P101 -133.2(4) . . . . ?
C103 N104 C105 C106 59.3(6) . . . . ?
C205 N204 N38 P201 122.0(4) . . . . ?
C205 N204 C203 C202 -61.1(6) . . . . ?
C205 C206 C213 O205 -172.7(4) . . . . ?
C202 O201 C206 C205 56.6(5) . . . . ?
C202 O201 C206 C213 177.4(5) . . . . ?
C202 N207 C208 O202 -4.5(10) . . . . ?
C202 N207 C208 N209 176.4(6) . . . . ?
C202 N207 C212 C211 -176.4(6) . . . . ?
C213 C206 C205 N204 -173.4(4) . . . . ?
C208 N207 C202 O201 -152.7(6) . . . . ?
C208 N207 C202 C203 86.2(7) . . . . ?
C208 N207 C212 C211 2.9(10) . . . . ?
C208 N209 C210 O203 -177.3(7) . . . . ?
C208 N209 C210 C211 2.1(11) . . . . ?
C108 N107 C102 O101 -136.8(5) . . . . ?
C108 N107 C102 C103 101.4(6) . . . . ?
C108 N107 C112 C111 -0.9(9) . . . . ?
C108 N109 C110 O103 176.5(7) . . . . ?
C108 N109 C110 C111 -3.3(10) . . . . ?
C212 N207 C202 O201 26.6(8) . . . . ?
C212 N207 C202 C203 -94.5(7) . . . . ?
C212 N207 C208 O202 176.2(7) . . . . ?
C212 N207 C208 N209 -2.9(10) . . . . ?
C210 N209 C208 N207 0.3(11) . . . . ?
C210 N209 C208 O202 -178.7(8) . . . . ?
C203 N204 N38 P201 -114.7(4) . . . . ?
C203 N204 C205 C206 59.8(6) . . . . ?
